62691-70-7

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 5-Bromo-2-oxopentanoate is used as a key intermediate in the synthesis of D471015, a compound with potential therapeutic applications. Its role in the synthesis process is crucial for the development of new drugs and treatments in the pharmaceutical industry.
Used in Metabolic Research:
As a metabolite of asymmetric dimethylarginine, Methyl 5-Bromo-2-oxopentanoate is also used in metabolic research to study the pathways and mechanisms involved in the metabolism of Methyl 5-broMo-2-oxopentanoate. This research can contribute to a better understanding of various metabolic processes and the development of targeted therapies for related conditions.

Upstream product

• 67-56-1 methanol 
• 110977-73-6 α-ethoxalyl-γ-butyrolactone 
• 61427-27-8 methyl 2-hydroxy-5-bromo-pentanoate 
• 7664-93-9 sulfuric acid 
• 7732-18-5 water 
• 42564-36-3 oxo-(2-oxotetrahydrofuran-3-yl)acetic acid ethyl ester 
• 57224-27-8 5-bromo-2-oxopentanoic acid 

Downstream Products

• 452336-73-1 methyl 5-dibenzylphosphonoxy-2,2-dimethoxypentanoate 
• 85851-98-5 6-methoxy-1-phenyl-1-(2-pivaloylamidophenyl)-2,3-hexanedione 
• 85852-01-3 1-methoxy-6-phenyl-6-(2-pivaloylamidophenyl)non-8-ene-4,5-dione 
• 85851-99-6 2-allyloxy-6-methoxy-1-phenyl-1-(2-pivaloylamidophenyl)hex-1-en-3-one 
• 85851-97-4 3,3,6-trimethoxy-1-phenyl-1-(2-pivaloylamidophenyl)-2-hexanone 
• 107347-90-0 α-keto-δ-(N^G,N^G-dimethylguanidino)valeric acid 
• 1019648-12-4 C₁₃H₁₆BrNO₃ 

Relevant academic research and scientific papers

Production process of 5-(3, 3-dimethylguanidino)-2-oxopentanoic acid

The invention discloses a production process of 5-(3,3-dimethylguanidino)-2-oxopentanoic acid. The 5-(3,3-dimethylguanidino)-2-oxopentanoic acid is prepared by connecting two fragments; the first fragment is prepared by the following steps: carrying out a substitution reaction on diethyl oxalate, serving as an initial raw material, and 1,4-butyrolactone to generate an intermediate 1, carrying outa ring-opening bromination reaction on the intermediate 1 and an acetic acid solution of hydrobromic acid to obtain an intermediate 2, and carrying out an esterification reaction on the intermediate 2and methanol to prepare an intermediate 3; and the second fragment is prepared by reacting N,N'-bis-BOC-1H-1-guanidinopyrazole serving as an initial raw material with a methanol solution of dimethylamine to obtain an intermediate 4. An alkylation substitution reaction on the intermediates 4 and 3 to prepare an intermediate 5, the intermediate 5 is deprotected to obtain an intermediate 6, and ester is hydrolyzed to obtain the target product. By establishing strict internal control standards for initial raw materials and intermediates and strictly controlling key process step parameters, the qualified product can be stably prepared in multiple batches.

Exploring symmetry-based logic for a synthesis of Palau'amine

(Chemical Equation Presented) A synthetic approach to palau'amine is described that exploits veiled symmetry in the structure. Bis-alkylidenes i have been prepared and found susceptible to halogenative desymmetrization using t-BuOCl. This oxidation forms

Preparation of α,α-disubstituted α-amino acid derivatives via alkyl addition to α-oxime esters with organozinc species

An α-oxime ester derivative prepared via treatment of an acetylenedicarboxylate or an α-keto ester with hydroxylamine underwent C-alkylation to the C=N bond of the oxime group by a Lewis-acid-promoted reaction with a trialkylzincate or a dialkylzinc reagent. The O-N bond of the thus obtained adduct was reductively cleaved under hydrogenolysis in the presence of the Pd-C catalyst to afford an α-amino ester. Treatment of the oxime derivative prepared from methyl 5-bromo-2-oxopentanoate with the trialkylzincate gave an α-alkyl proline derivative via the addition reaction followed by the intramolecular attack upon a bromine-bearing carbon. The reaction of ethyl 4-oxo-2-pentynoate with hydroxylamine formed an isoxazole derivative by way of the intramolecular attack of an in situ-generated oxime to the carbonyl group. From this isoxazole derivative, ethyl 2-amino-4-oxo-2- pentenoate was given by the Pd-C-catalyzed hydrogenolysis. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Design, synthesis, and evaluation of 6-carboxyalkyl and 6-phosphonoxyalkyl derivatives of 7-oxo-8-ribitylaminolumazines as inhibitors of riboflavin synthase and lumazine synthase

A series of 6-carboxyalkyl and 6-phosphonoxyalkyl derivatives of 7-oxo-8-D-ribityllumazine were synthesized as inhibitors of both Escherichia coli riboflavin synthase and Bacillus subtilis lumazine synthase. The compounds were designed to bind to both the ribitylpurine binding site and the phosphate binding site of lumazine synthase. In the carboxyalkyl series, maximum activity against both enzymes was observed with the 3′-carboxypropyl compound 22. Lengthening or shortening the chain linking the carboxyl group to the lumazine by one carbon resulted in decreased activity. In the phosphonoxyalkyl series, the 3′-phosphonoxypropyl compound 33 was more potent than the 4′-phosphonoxybutyl derivative 39 against lumazine synthase, but it was less potent against riboflavin synthase. Molecular modeling suggested that the terminal carboxyl group of 6-(3′-carboxypropyl)-7-oxo-8-D-ribityllumazine (22) may bind to the side chains of Arg127 and Lys135 of the enzyme. A hypothetical molecular model was also constructed for the binding of 6-(2′-carboxyethyl)-7-oxolumazine (15) in the active site of E. coli riboflavin synthase, which demonstrated that the active site could readily accommodate two molecules of the inhibitor.

Bicycloheptane substituted diamide and its congener prostaglandin analogs

Bicycloheptane substituted amide prostaglandin analogs are provided having the structural formula STR1 wherein m is 0 to 4; A is --CH=CH-- or --CH2 --CH2 --; n is 1 to 5; Q is --CH=CH--, --CH2 --, STR2 or a single bond; R is CO2 H, CO2 alkyl, CO2 alkali metal, CO2 polyhydroxyamine salt, --CH2 OH, STR3 wherein R4 and R5 are the same or different and are H, lower alkyl, hydroxy, lower alkoxy or aryl, at least one of R4 and R5 being other than hydroxy and lower alkoxy; p is 1 to 4; R1 is H or lower alkyl; q is 1 to 12; R2 is H or lower alkyl; and R3 is H, lower alkyl, lower alkenyl, lower alkynyl, aryl, arylalkyl, lower alkoxy, aryloxy, arylalkyloxy, amino, alkylamino arylamino, arylalkylamino, lower alkyl-S-, aryl-S-, arylalkyl-S-, STR4 (wherein n' is 0, 1 or 2), alkylaminoalkyl, arylaminoalkyl, arylalkylaminoalkyl, alkoxyalkyl, aryloxyalkyl or arylalkoxyalkyl. The compounds are cardiovascular agents useful, for example, in the treatment of thrombotic disease.

7-OXABICYCLOHEPTANE SUBSTITUTED DIAMIDE AND ITS CONGENER PROSTAGLANDIN ANALOGS USEFUL IN THE TREATMENT OF THROMBOTIC DISEASE

7-Oxabicycloheptane substituted amide prostaglandin analogs are provided having the structural formula STR1 wherein m is 0 to 4; A is--CH=CH--or--CH 2--CH 2--; n is 1 to 5; Q is--CH=CH--,--CH 2--, STR2 or a single bond; R is CO 2 H, CO 2 alkyl, CO 2 alkali metal, CO 2 polyhydroxyamine salt,--CH 2 OH, STR3 wherein R. sup.4 and R 5 are the same or different and are H, lower alkyl, hydroxy, lower alkoxy or aryl, at least one of R 4 and R 5 being other than hydroxy and lower alkoxy; p is 1 to 4; R. sup.1 is H or lower alkyl; q is 1 to 12; R 2 is H or lower alkyl; and R 3 is H, lower alkyl, lower alkenyl, lower alkynyl, aryl, arylalkyl, lower alkoxy, aryloxy, arylalkyloxy, amino, alkylamino arylamino, arylalkylamino, STR4 (wherein n' is 0, 1 or 2), alkylaminoalkyl, arylaminoalkyl, arylalkylaminoalkyl, alkoxyalkyl, aryloxyalkyl or arylalkoxyalkyl.The compounds are cardiovascular agents useful, for example, in the treatment of thrombotic disease.

7-oxabicycloheptane substituted sulfonamide prostaglandin analogs

7-Oxabicycloheptane substituted sulfonamide prostaglandin analogs are provided having the structural formula STR1 wherein m is 0 to 4; A is --CH=CH-- or --CH2 --CH2 --; n is 1 to 5; Q is --CH=CH--, --CH2 --, STR2 or a single bond; R is CO2 H, CO2 alkyl, CO2 alkali metal, CO2 polyhydroxyamine salt, --CH2 OH, STR3 wherein R3 and R4 are the same or different and are H, lower alkyl or aryl; p is 1 to 4; R1 is H or lower alkyl; and R2 is H, lower alkyl, lower alkenyl, lower alkynyl, aryl, arylalkyl, cycloalkyl or cycloalkylalkyl. The compounds are cardiovascular agents useful, for example, in the treatment of thrombotic disease.

7-oxabicycloheptane substituted keto-amide prostaglandin analogs useful in the treatment of thrombotic disease

7-Oxabicycloheptane substituted keto-amide prostaglandin analogs are provided having the structural formula STR1 wherein m is 0 to 4; A is --CH=CH-- or --CH2 --CH2 --; n is 1 to 5; Q is --CH=CH--, --CH2 --, STR2 or a single bond; R is CO2 H, CO2 alkyl, CO2 alkali metal, CO2 polyhydroxyamine salt, STR3 wherein R4 and R5 are the same or different and are H, lower alkyl, hydroxy, lower alkoxy or aryl, at least one of R4 and R5 being other than hydroxy and lower alkoxy; p is 1 to 4; R1 is H or lower alkyl; and R2 is H, lower alkyl, lower alkenyl, aryl, arylalkyl, cycloalkyl or cycloalkylalkyl. The compounds are cardiovascular agents useful, for example, in the treatment of thrombotic disease.

7-oxabicycloheptane substituted thioamide-amide prostaglandin analogs

7-Oxabicycloheptane substituted thioamideamide prostaglandin analogs are provided having the structural formula STR1 wherein m is 0 to 4; A is --CH=CH-- or --CH2 --CH2 --; n is 1 to 5; Q is --CH=CH--, --CH2 --, STR2 or a single bond; R is CO2 H, CO2 alkyl, CO2 alkali metal, CO2 polyhydroxyamine salt, --CH2 OH, wherein R4 and R5 are the same or different and are H, lower alkyl, hydroxy, lower alkoxy or aryl, at least one of R4 and R5 being other than hydroxy and lower alkoxy; p is 1 to 4; R1 is H or lower alkyl; q is 1 to 12; and R2 R3 are the same or different and are H, lower alkyl, lower alkenyl, lower alkynyl, aryl, arylalkyl, lower alkoxy, aralkyloxy, cycloalkyl or cycloalkylalkyl. The compounds are cardiovascular agents useful, for example, in the treatment of thrombotic disease.

7-oxabicycloheptane substituted diacid diamide prostaglandin analogs

7-Oxabicycloheptane substituted diacid diamide prostaglandin analogs are provided having the structural formula STR1 wherein m is 0 to 4; A is --CH=CH-- or --CH2 --CH2 --; n is 1 to 5; Q is --CH=CH--, --CH2 --, STR2 or a single bond; R is CO2 H, CO2 alkyl, CO2 alkali metal, CO2 polyhydroxyamine salt, --CH2 OH, STR3 wherein R4 and R5 are the same or different and are H, lower alkyl, hydroxy, lower alkoxy or aryl, at least one of R4 and R5 being other than hydroxy and lower alkoxy; p is 1 to 4; R1 is H or lower alkyl; q is 1 to 12; R2 and R3 are the same or different and are H, lower alkyl, lower alkenyl, lower alkynyl, aryl, arylalkyl, lower alkoxy, aralkyloxy or cycloalkyl. The compounds are cardiovascular agents useful, for example, in the treatment of thrombotic disease.